Novel metabolic pathway of phenols catalyzed by cytochrome P450 and its mechanism

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Abstract

We have found a novel metabolic pathway of phenols catalyzed by cytochrome P450 and its chemical models. When various p-substituted phenols (substituent = OPh, NO2, CN, CH2OH, COCH3, COPh, COOH, F, Cl, and Br) were reacted with rat liver microsomes system or meso-tetraphenylporphinatoiron(III) chloride model system, the substituent was eliminated to produce hydroquinone. In the case of p-cresol, p-toluquinol was formed instead of hydroquinone. To elucidate how the substituent is eliminated, we attempted to detect the product derived from the eliminated group. Results indicated that the mechanism of this reaction can be divided into two types: the substituent is eliminated as an anion and as a cation. P450 also catalyzed phenol coupling reaction to give biphenyl derivatives, diphenyl ether derivatives, and dibenzodioxin.

Original languageEnglish
Pages (from-to)1202-1209
Number of pages8
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume58
Issue number12
DOIs
Publication statusPublished - 2000 Dec

Keywords

  • Cytochrome P450
  • Cytochrome P450 model
  • Dibenzodioxin
  • Drug metabolism
  • Estrogen
  • Phenol coupling
  • Phenol metabolism

ASJC Scopus subject areas

  • Organic Chemistry

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